10 Movies & Shows Similar to Head Over Heels (2025)

Description: A precursor to 'Head Over Heels (2025)', 'Sex and the City' set the standard for shows about female friendship, love, and career struggles in a big city. Both shows feature stylish, independent women navigating the ups and downs of relationships with humor and honesty.

Fact: The iconic opening sequence was shot in just one day. Sarah Jessica Parker initially turned down the role of Carrie Bradshaw. The show was based on Candace Bushnell's book of the same name, which was a collection of her newspaper columns.

Description: Similar to 'Head Over Heels (2025)', 'The Mindy Project' is a romantic comedy that blends humor with heartfelt moments. Both shows feature strong, quirky female leads who are unapologetically themselves while navigating the complexities of love and career.

Fact: Mindy Kaling wrote, produced, and starred in the show, making her one of the few women of color to do so in Hollywood. The show was originally canceled by Fox after three seasons but was picked up by Hulu for three more seasons. Chris Messina, who played Danny Castellano, was initially hesitant to take the role because he didn't want to play another 'jerk' character.

Description: Similar to 'Head Over Heels (2025)', 'Broad City' is a comedy about female friendship and the absurdities of life in a big city. Both shows feature quirky, relatable protagonists who navigate life's challenges with humor and resilience.

Fact: The show started as a web series created by Ilana Glazer and Abbi Jacobson. Amy Poehler served as an executive producer for the TV adaptation. The series finale featured a cameo by Hillary Clinton.

Description: Like 'Head Over Heels (2025)', 'Younger' is a witty, romantic comedy-drama that delves into themes of identity, reinvention, and the complexities of modern relationships. Both shows blend humor with heartfelt moments, appealing to audiences who enjoy character-driven stories with a touch of glamour.

Fact: The show is based on the novel of the same name by Pamela Redmond Satran. Sutton Foster, who plays Liza, is a two-time Tony Award-winning actress. The series was originally intended to be a movie, but was developed into a TV show instead.

Description: Like 'Head Over Heels (2025)', 'Jane the Virgin' is a romantic comedy-drama that blends humor, heart, and a touch of melodrama. Both shows feature strong female protagonists navigating love, family, and career in a modern, multicultural setting.

Fact: The show is based on the Venezuelan telenovela 'Juana la Virgen'. Gina Rodriguez, who plays Jane, won a Golden Globe for her performance. The show is known for its unique storytelling style, which includes a narrator and dramatic plot twists.

Description: Similar to 'Head Over Heels (2025)', 'Crazy Ex-Girlfriend' is a musical comedy-drama that explores themes of love, mental health, and self-discovery with humor and heart. Both shows feature quirky, relatable protagonists who are unafraid to be themselves.

Fact: Rachel Bloom, who created and starred in the show, won a Golden Globe for her performance. The show features original songs in every episode, which Bloom co-wrote. The series was praised for its honest portrayal of mental health issues.

Description: Like 'Head Over Heels (2025)', 'Insecure' explores the complexities of modern relationships, female friendship, and personal growth with a mix of humor and raw honesty. Both shows feature relatable, flawed protagonists who are trying to figure out life and love.

Fact: The show is based on Issa Rae's web series 'Awkward Black Girl'. Issa Rae and Larry Wilmore co-created the show. The series was praised for its authentic portrayal of Black women's experiences.

Description: Like 'Head Over Heels (2025)', 'Fleabag' is a dark comedy that explores themes of love, loss, and self-discovery with sharp wit and emotional depth. Both shows feature complex female protagonists who break the fourth wall to share their inner thoughts with the audience.

Fact: Phoebe Waller-Bridge wrote and starred in the show, which is based on her one-woman play. The show won six Emmy Awards, including Outstanding Comedy Series. Waller-Bridge has stated that she has no plans to continue the series beyond its second season.

Description: Similar to 'Head Over Heels (2025)', 'The Marvelous Mrs. Maisel' is a stylish, witty show about a woman navigating love, career, and personal growth. Both shows feature strong female leads who challenge societal expectations with humor and determination.

Fact: The show was created by Amy Sherman-Palladino, who also created 'Gilmore Girls'. Rachel Brosnahan, who plays Midge Maisel, had to learn how to perform stand-up comedy for the role. The show has won numerous awards, including multiple Emmys and Golden Globes.

Description: Similar to 'Head Over Heels (2025)', 'The Bold Type' explores themes of female friendship, career ambitions, and romantic entanglements in a modern urban setting. Both shows feature strong, relatable female protagonists navigating personal and professional challenges with humor and heart.

Fact: The show was inspired by the life of Joanna Coles, the former editor-in-chief of Cosmopolitan magazine. The character Sutton Brady was originally written as a straight woman, but the actress Meghann Fahy suggested making her bisexual, which the writers incorporated into the storyline. The show was canceled after five seasons due to declining ratings, but it remains a fan favorite for its empowering messages.